I've read a few articles about ageism and wisdom lately.
It's disappointing because people always say the same thing, and they always
don't get anywhere. Young people say "Wisdom comes with experience, not
age!" and old people say "You'll understand when you grow up!" and the cycle
repeats, forever.

I'm in my thirties now (which makes me "old", ha ha, at least by the
definition programmers use). The theme of this diary is "things I recently
learned that I wish someone had told me sooner," and so with that in mind,
here are a few things I understood when I grew up, around age 30 or so.

First of all, you have to actually define wisdom. Wisdom is not
productivity. It's not being smart. It's not being successful, or even a
proxy for being successful. Wisdom is not the same as insight, although
that's getting closer. Wisdom is not the same as mere experience. The
Hollywood symbol for wisdom is a homeless, disabled, ancient, wrinkled,
Chinese guy in a martial arts movie, sitting on a street corner muttering
aphorisms without using the words "the" or "a". And that, I think, is
really the closest to what we mean by wisdom.

Wisdom is knowing what the movie will be about, and how it will probably
end, five minutes in, before the plot has even started. And then
wisdom is the self control to only tell the hero exactly the part he needs
to hear.

Let's pull this out of Hollywood and back to programming. I'm going to
dumb that down a bit and put it like this: wisdom is the ability to predict
the future.

You might have heard that "The best way to predict the
future is to invent it," a famous statement by famous old wise guy Alan
Kay. But according to that link, he said it when he was 29 or 30. That
quote is partly true (what you can control, you can predict), but it's the
perfect wishful thinking of a young person trying to rationalize away the
need for wisdom.

As you gain wisdom, you can begin to predict even the things you
can't control. You might think you can accomplish the same thing
with facts, logic, and a really big search engine, but you can't. You can
predict some things that way, but not most things. Maybe someday, after all
the rest of Artificial Intelligence is finished, we can have Artificial
Wisdom. Wisdom is the thing your computer doesn't do. To become
wise, you have to train your intuition using your physical senses. That
takes time, and it actually takes actually physically being there to know
what it feels like. People who think they can be wise without
feeling it are idiots. You can be lots of things without feeling the
world, including successful, rich, famous, productive, and smart. But you
can't be wise.

So far, this is just a hopeless rant about how you're just too young to
understand. Let's take it past that. I can't make you wise, but maybe I
can help you spot wisdom when you see it. For me, learning to spot it was
the first step in learning to get it.

I co-founded my first company when I was 19 or 20 (depending how you define
"founded") and surely lacking in wisdom, because wise people don't start
tech companies. A couple of years later, after me and my technical
co-founder had built and sold the first version of the product (to some
small profit, comparable to taking a paid internship instead), we found some
experienced businesspeople who joined in order to handle the business side.
This was a smart (not to say wise) choice on our part. The new people were
a few years older than us and lacked wisdom too, but had experience. They
got us angel funding, then venture capital, and ramped our sales into the
millions of dollars per year.

Shortly after our first meeting with those new businesspeople, one of them
presented the rest of us a simple one-page "getting on the same page" memo
of understanding. (Not a complicated MOU like lawyers draw up, just a
simple letter in his own words.) Not knowing anything about business, I
found a businessperson I knew (friend of a friend) to show the letter to.
He was an older guy. His 30-second review was, "Stay away from this guy.
He isn't the kind of person you want to be dealing with." I ignored him,
because that's what young people do with advice they don't like.

Roughly 8 years later, we sold our company to IBM for untold (I can't tell
you) zillions (not a real word) of dollars. The venture capitalists, who
everyone teaches you to fear and distrust, were respectful, ethical, and
fair during the entire time we spent working with them. (In particular
Desjardins-Innovatech were great.) This business guy, however, the one who
wrote the memo, turned out to be a slimeball. To this day, he is still the
only person on my "do not treat as human" blacklist. I had to create my
blacklist for this purpose. But that's another story for another day.

The point is, 5 minutes into my story, someone older, who turned out to be
wise, had this guy pegged after reading half a page of text, without even
meeting him. He predicted the future, accurately, instantly, and without
any real facts. That's either luck or wisdom.

And so we come to our next problem. I hope what you take away from this
article won't be, "Listen to old people, they know stuff," because that
would be stupid. Most old people, like most young people, are dumb, and so
taking their advice is dumb. Numerous people told me the product we were
building was physically impossible and to maybe try something that made
sense and that people wanted, and they were all 100% wrong, and I was right
to ignore them. (Maybe less right to tell them so to their face, but oh
well, something something wisdom etc.)

No, we're not done yet. All that was just to say, yes, wisdom exists, and
no, you probably don't have it. But I want you to know that you can, at
least, make a series of observations in order to hypothesize about its
nature. You can't see protons either, but you know they're there.

There have been a few very memorable moments of my life when I have acquired
a few Real Actual Nuggets1 of Wisdom. I know these moments,
because they were so astonishingly blatant. I guess there were probably
other, subtler ones, but let's ignore those, because I can offer no advice
on how to detect them. I think the big ones are enough. With those ones,
looking back on my life, I can see the before-wisdom-nugget version of me,
and the after-wisdom-nugget version of me. The after-nugget version is
dramatically better at predicting the future.

Perhaps my biggest, most multi-faceted wisdom acquisition event was reading
and understanding Crossing the
Chasm, a book from 1991 about companies from before 1991. Yeah,
sure, it taught me all sorts of stuff about why my company wasn't growing
exponentially, which was great to know, and explained in retrospect how much
of our time we'd been wasting on stupid initiatives, which was embarrassing
but also great to know. But as part of discovering those things - and
probably in a moment of weakness caused by it - I learned something else.

All those problems we were having? They'd been had by people for decades.
And people already knew how to solve them.

When we did finally sell our company, IBM bought it because of about 5% of
the stuff it contained. The other 95% was great stuff, but it wasn't what
IBM wanted. In Crossing the Chasm terms, we had finally, 9 years in,
created a "Whole Product" for a "Target Market." We could have accomplished
the same thing, I think, with only 5% of the work, if only we had known
which 5%.

You will try to tell me that there was no way to know which 5%. That the
other 95% of wasted effort was necessary as part of the experiment. I would
have told you that, too, back then. Back before I knew it was
false.2

That was the big lesson about wisdom for me, the one that has put all these
discussions about young vs old and energetic vs experienced into
perspective. In 1999, there was nobody whose experience would tell you how
to build a Linux-based server appliance that would sell like hotcakes. But
there were people who could tell you we were doing it wrong, and
explain exactly why and how, in step-by-step detail, including the totally
predictable consequences of our mistakes (correct) and instructions about
how to do it right. They published a book about it in 1991, before Linux
even existed. It said, "You are doing this. You should do that instead."
And they were exactly right, on both counts.

Young people have energy. We had a lot of energy, and produced a lot of
super crazy amazing stuff that I'm still very proud of today. But we lacked
wisdom, so 95% of it was wasted. My goal is no longer to code 10x as fast
as the average programmer; my goal is to not have 19/20 of my production be
useless.

So here is my first nugget of wisdom, purified and cleaned up and presented
with that huge preface. It was the one that got me on the long, slow,
painful path to maybe learning other ones someday. Maybe it will help you
too.

If you think nobody has ever done this before, you are almost
certainly wrong. Many people have done it before. Most of them have done
it wrong. Find the ones who did it right, and find out how they knew it was
right. If you can learn to find wisdom in others, someday you can find
wisdom in yourself.

I know what it feels like to be 20 and running a startup. You have faith in
yourself, and you feel like your world is unique, and nobody else has the
same problems you do. You certainly feel like experiences from 20 years ago
can't possibly be relevant. Once you've learned otherwise, then, laddie,
then maybe we can talk.

Footnotes

Whenever I try to type "nuggets" I keep typing "nuggles." I hope this
footnote has been educational for you.

I'm not trying to be a "Customer Development denier" here. There will
always be inefficiencies caused by searching for a business model. But if
you spend 9 years and 95% of your work is wasted, you're doing it wrong.